ITunes doesn't recognize iPod

Question

I'll start out by saying that I've hurled every curse I can imagine out into the inky blackness of space the past four weeks. I've pulled out hair, gnashed teeth, thrown chairs, punched walls, and have almost gone nuclear.
I have a laptop. External harddrive. 8000 songs, most of which are ripped from many CDs in my collection as a past DJ. It takes many nights of importing CDs to get here. Since I bought my first of three iPods in 2005 I've bought around $2000 from the iTunes store. Along the way I've burned up one harddrive, got no sympathy from the Genius Store for transferring songs to the new hardrive and had to use 3rd party software.
My default library location is on my external drive. I also consolidated my library. Yet, every two months or so, iTunes forgets that F: is my library location and thinks it is now C:. I now have thousands of broken links and lost playlists. After the dozenth time this happend I said no more to iTunes and I tried various other players and finally settled on MediaMonkey. It worked great and does a lot more as a program.
Yet there were problems in syncing my songs through mediamonkey. Songs and playlist were there but when I tried to play it on my iPod, only some of them would play and it would skip through the other songs. Finally, after hours of trying to make it work, I grudgingly went back to iTunes with much gnashing of teeth and wailing and cursing.
My iPod synced okay... and then about a week later of using only iTunes it stopped syncing halfway through a sync. It would suddenly tell me that it could not read from the IPOD and I should restore it.
I did.
Well... Another four nights of several hours each night of doing the 5 R's over and over yielded nothing. Zilch. I've reset the iPod, installed iTunes, over and over. I've checked drivers, uninstalled programs, disabled drivers and enabled, restarted rebooted, and done everything on every page I could find via GOOGLE save kill a chicken in a voudou ritual.
My iPhone synced just fine. My iPod showed up on MY COMPUTER. The icon shows up in iTunes. But it tells me to restore... ALWAYS.
I've renamed my USB drive (my iPod used to be E: and now it is P:). I've put it in external drive use and back out. I've installed the Windows Super Uninstall Cleaner program and killed anything Apple related on my computer with impunity again and again. I've run registry cleaners and other cleaning tools. Nothing worked.
The only other option left was to sign my soul over to the devil who was now sitting in the corner and grinning profusely, and I decided to go back to mediamonkey and try to use it. I turned it on and saw that, with my iPod connected, I had three options under the sync menu, E: iPod, E: iPod classic, and E: external hard drive. I tried syncing a 2 Live Crew CD to both options that said iPod but while it gave me the option under the menu tab, the icon wasn't lit up (meaning it wasn't there). So I chose the third option, external harddrive. When I did this the icon lit up and it synced the songs for me.
Weird part here. When I disconnected the iPod and looked for the songs... there was nothing there. Zilch (I did have the option to organize in iTunes fashion checked as well). When I plugged the iPod back in and iTunes started, it asked me to name my new iPod and started syncing happily away.
Currently it is a couple hundred through the list of songs to sync and I am still waiting with baited breath to see if it works.
This is very weird and I have no idea what happened but hope that if someone else reads this that they will not jump off that building, as I almost did, but will try something else. I hope this helps some computer programmer find the glitch that seems to be plaguing so many iPod users (there are tons of pages out there on this problem).
Good luck!

Answer 1

Windows does not appear in iTunes
http://docs.info.apple.com/article.html?artnum=93716
I'm still trying to find any suggestions to give you about shuffling. You might have to restore your iPod to factory settings if multiple reset attempts did not work. Be sure to back up your music before you do that.